Palladium-Catalyzed Regioselective [3+2] Cycloadditions of α,β-Unsaturated Imines with Vinylethylene Carbonates: Access to Oxazolidines

被引：0

作者：

Wang, Yuanbo ^{[1
]}

Wang, Yue ^{[2
]}

Sun, Tong ^{[1
]}

Liu, Qinglin ^{[1
]}

Li, Er-Qing ^{[1
]}

机构：

[1] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Peoples R China

[2] Henan Univ Technol, Coll Adv Interdisciplinary Sci & Technol CAIST, Zhengzhou 450001, Peoples R China

来源：

CATALYSTS | 2024年 / 14卷 / 08期

基金：

中国国家自然科学基金;

关键词：

palladium catalysis; 3+2] cycloaddition; alpha; beta-unsaturated imines; vinylethylene carbonates; oxazolidines; DECARBOXYLATIVE CYCLOADDITION; CONSTRUCTION; ANNULATION; YLIDES;

D O I：

10.3390/catal14080508

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

We reported palladium-catalyzed regioselective [3+2] cycloadditions of alpha,beta-unsaturated imines with vinylethylene carbonates, providing the desired oxazolidines in moderate-to-high yields. This reaction provides a facile route for the highly regioselective synthesis of functional oxazolidines. The synthetic utility of the current method was also demonstrated by a gram-scale reaction.

引用

页数：12

共 35 条

[1] Utilizing Palladium-Stabilized Zwitterions for the Construction of N-Heterocycles
Allen, Benjamin D. W.
Lakeland, Christopher P.
Harrity, Joseph P. A.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (56) : 13830 - 13857
[2] Oxazolidines from Neocalyptrocalyx longifolium Inhibit MsrA Protein in Methicillin Resistant Staphylococcus aureus
de Souza, Thalisson Amorim
Silva, Joanda Paola Raimundo
Rodrigues, Damara Freitas
Herrera-Acevedo, Chonny
de Menezes, Renata Priscila Barros
Borges, Nathalie Hellen
de Melo, Jose Iranildo Miranda
de Siqueira-Junior, Jose Pinto
Scotti, Marcus Tullius
Abreu, Lucas Silva
Tavares, Josean Fechine
da Silva, Marcelo Sobral
[J]. REVISTA BRASILEIRA DE FARMACOGNOSIA-BRAZILIAN JOURNAL OF PHARMACOGNOSY, 2023, 33 (05): : 1084 - 1088
[3] Diversity-Orientated Stereoselective Synthesis through Pd-Catalyzed Switchable Decarboxylative C-N/C-S Bond Formation in Allylic Surrogates
Deng, Lei
Kleij, Arjan W.
Yang, Weibo
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (72) : 19156 - 19161
[4] Recent advances of Pd-π-allyl zwitterions in cycloaddition reactions
Du, Juan
Li, Yun-Fan
Ding, Chang-Hua
[J]. CHINESE CHEMICAL LETTERS, 2023, 34 (11)
[5] Palladium-catalyzed stereoselective (3+2) cycloaddition of vinylethylene carbonates with cyclic N-sulfonyl ketimines
Gao, Xing
Zhu, Dongyu
Jiang, Feng
Liao, Jianning
Wang, Wei
Wu, Yongjun
Zheng, Lufei
Guo, Hongchao
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (22) : 4877 - 4881
[6] Palladium-Catalyzed [5+2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes
Gao, Xing
Zhu, Dongyu
Chen, Yuehua
Deng, Hao
Jiang, Feng
Wang, Wei
Wu, Yongjun
Guo, Hongchao
[J]. ORGANIC LETTERS, 2020, 22 (18) : 7158 - 7163
[7] Enantio- and Diastereoselective Synthesis of β-Aryl-β-pyrazolyl α-Amino Acid Esters via Copper-Catalyzed Reaction of Azomethine Ylides with Benzylidenepyrazolones
Gong, Yan-Chuan
Wang, Yue
Li, Er-Qing
Cui, Hao
Duan, Zheng
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (06) : 1389 - 1393
[8] Recent Advances in Palladium-Catalyzed [4+n] Cycloaddition of Lactones, Benzoxazinanones, Allylic Carbonates, and Vinyloxetanes
Guo, Mengyan
Zhang, Panke
Li, Er-Qing
[J]. TOPICS IN CURRENT CHEMISTRY, 2023, 381 (06)
[9] Catalytic Transformations of Functionalized Cyclic Organic Carbonates
Guo, Wusheng
Enrique Gomez, Jose
Cristofol, Alex
Xie, Jianing
Kleij, Arjan W.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (42) : 13735 - 13747
[10] Organocatalytic Asymmetric Inverse-Electron-Demand Aza-Diels-Alder Reaction of N-Sulfonyl-1-aza-1,3-butadienes and Aldehydes
Han, Bo
Li, Jun-Long
Ma, Chao
Zhang, Shan-Jun
Chen, Ying-Chun
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (51) : 9971 - 9974

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